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Historic Downtown Garden Oasis with Private Patio

Apartment in Chestertown with kitchenette and balcony

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Photo gallery for Historic Downtown Garden Oasis with Private Patio

Outdoor dining
Fridge, microwave, coffee/tea maker, electric kettle
Interior
Interior
1 bedroom, free WiFi, bed sheets

Reviews

10 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 2525 sq ft

Popular amenities

  • Kitchen
  • Air conditioning
  • Outdoor Space
  • Parking available
  • Barbecue grill

Explore the area

View in a map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪3 min walk‬
  • Place, Wilmer Park
    ‪6 min walk‬
  • Place, Washington College
    ‪8 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪106 min drive‬

Room options

About the neighborhood

Chestertown

This apartment places you next to River Arts Chestertown and within a 10-minute walk of Garfield Center for the Arts at the Prince Theater. The apartment includes a kitchenette, a balcony, and a dining area.
View more Apartments in ChestertownOpens in a new window

What's nearby

  • River Arts Chestertown - 3 min walk - 0.2 miles
  • Wilmer Park - 6 min walk - 0.4 miles
  • Washington College - 8 min walk - 0.4 miles
  • Historical Society of Kent County Maryland - 8 min walk - 0.5 miles
  • Chestertown Historic District - 8 min walk - 0.5 miles

Getting around

  • Baltimore, MD (MTN-Martin State) - 93 min drive

Restaurants

  • ‪Royal Farms - ‬6 min walk
  • ‪Dunkin - ‬3 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Procolino's - ‬3 min drive
  • ‪7-Eleven - ‬7 min walk

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

Historic Downtown Garden Oasis with Private Patio

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!

Our guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill.

We are proud to give back to our town through the renting of our guesthouse. Five percent of our gross revenue is donated to one or more local non-profits annually. Additionally, the guesthouse features artwork from local artists and galleries, and you'll find home goods and products from nearby shops.

Our place is designed to provide you with everything you need for a comfortable stay, including fast wifi, a private entrance with self check-in via keyless entry, and free street or off-street parking.

You'll find all the essentials like towels, bed sheets, soap, and toilet paper, as well as a hairdryer, cleaning products, shampoo, conditioner, and body soap. There are extra pillows and blankets, and hangers to store your clothes.

The guesthouse has two brand new air conditioning and heating units that you control, so you will be comfortable year-round.

Safety is a top priority, so we have a smoke and carbon monoxide alarm, a fire extinguisher, and a first aid kit on hand. Additionally, for awareness, there is a Ring Video Doorbell installed on the front door of the primary house. It is used to monitor our front door but not the door of the guest unit.

In the kitchenette, you'll find a microwave, dishes, silverware, cups, a mini-fridge with freezer, a hot water kettle, a coffee maker (both a Keurig and a Nespresso), wine glasses, and a toaster.

During your stay you will have exclusive access to the following rooms and spaces:

- Bedroom
- Full bathroom
- Kitchenette
- Living room
- Dining area
- Patio

Additionally, you'll be sharing the backyard with us, but we'll do our best to give you privacy during your stay.

If you have any questions or concerns about the areas you can access, or if you need any additional information about your stay, please don't hesitate to ask.

We're committed to providing our guests with an exceptional experience, and we're always available to answer any questions or provide recommendations to help make your stay unforgettable.

Here's what some of our recent guests have said about their stay:

"Perfect apartment-type accommodation located in a lovely walkable town. These hosts literally thought of a guest's every need... Besides being a comfortable, beautiful space top to bottom with an abundance of windows, the things that really stood out for us are: Self-check in keyless entry, gallery artwork throughout; large stone-top table with chairs for eating, gathering, working, etc; coffee machine with Keurig AND Nespresso pods (WOW!)" - Cindy

"Their place was exactly what I was looking for! It was clean, cute, centrally located, but yet private and offered everything I needed for my stay! I loved the special touches from the local businesses, the espressos, coffee, and tea options. Their place was spotless and the bed was extremely comfortable! They were also very responsive with any questions I had. If I ever come back to the area I will definitely stay at their place." - Megan

"Great place and location. Private and quiet, but walkable to restaurants of Chestertown. Comfortable and super clean! Very cute, indoors and out." - Joan

"Stephen and Marianna were delightful hosts for a perfect getaway weekend in Chestertown! Their detailed suggestions of local restaurants and events made our stay more enjoyable, as were their thoughtful messages to us during our stay to ensure that everything was going well. The apartment is such a gem tucked away in a courtyard at the back of their house in the historical section of town!" - Carla

We're confident that you'll love your stay at our guesthouse, and we can't wait to welcome you.

Book now to secure your spot!
The apartment is air-conditioned and features a kitchenette and a balcony or patio, and there's space to spread out with a separate bedroom and a dining area. Guests can expect to find free WiFi. Other standard amenities include a fenced private yard, a coffee maker, and a dining table.

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Property amenities

Internet

  • Available in the apartment: Free WiFi

Parking and transportation

  • Free offsite parking
  • Onsite parking includes off-street options

Kitchenette

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Freezer
  • Microwave
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 private bathroom
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Stereo

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Fully-fenced
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundromat nearby

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • In a rural location
  • In the city center
  • Near a hospital

Things to do

  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Local artist showcase
  • Unit size: 525 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

Guests can access their accommodation through a private entrance
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Remove personal items and remove leftover food and drinks
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.

Rules

There is a maximum stay of one month for Instant Bookings. For longer stays, please message the host first. Otherwise, your booking may be cancelled.
The max number of guests is two people. If you are two adults traveling with a child under 5, we can accommodate but you must let us know at booking.

Access methods

Private entrance

Pets

  • This property doesn't allow pets

Children and extra beds

  • Note from host: While not child friendly, we can accommodate.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 3:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25
Driving? This property offers free nearby parking.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Frequently asked questions

What's there to do around this apartment?

This apartment in Chestertown is within a 10-minute walk of Historical Society of Kent County Maryland, Chestertown Historic District, and Wilmer Park. You'll also find Garfield Center for the Arts at the Prince Theater and Sumner Hall less than a mile away.

Will I be able to park at this apartment?

No, there isn't parking at the apartment but you'll find free parking nearby.

Is this apartment adjacent to a casino?

No, this apartment is not connected to a casino.

Is there an indoor pool at this apartment?

No, there is no indoor pool at this apartment.

What do couples enjoy most about Historic Downtown Garden Oasis with Private Patio?

Couples staying at this apartment will value amenities like a kitchenette, kitchenettes in some apartments, as well as a garden.

Does Historic Downtown Garden Oasis with Private Patio have a hot tub?

No, this apartment doesn't have a spa tub.

Does this apartment include breakfast service?

No, this apartment doesn't offer breakfast.

Does this apartment allow pets to stay free of charge?

No, pets aren't allowed at this apartment.

What is the closest airport to this apartment?

The closest major airport to this apartment is Baltimore, MD (MTN-Martin State), which is about 20.6 mi away. Another top airport is Easton, MD (ESN-Easton - Newnam), which is around 27.5 mi away.

Are there rooms with balconies that I can book at Historic Downtown Garden Oasis with Private Patio?

Yes, every apartment at Historic Downtown Garden Oasis with Private Patio comes with a balcony.

Historic Downtown Garden Oasis with Private Patio Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 43 out of 45 reviews
Rating 8 - Good. 2 out of 45 reviews
Rating 6 - Okay. 0 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

10/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

9.4/10

Eco-friendliness

Reviews

10/10 Excellent

Kathleen M.

Liked: Cleanliness
Stayed 2 nights in Nov 2025

10/10 Excellent

Devan G.

Liked: Cleanliness
Everything was perfect and cozy. Stephen and Marianna are wonderful hosts and have anticipated all of our needs yet again. Their rental is inviting and beautifully appointed.
Stayed 3 nights in Dec 2025

10/10 Excellent

Judy C.

Liked: Cleanliness
Only wonderful things to say about this sweet apartment. First, the hosts, Stephen and Mariana, are incredibly hospitable and full of great ideas and recommendations for the area. This property is very clean and roomy (for two), has wonderful amenities and the hosts have thought of everything that makes this our go to place to stay when we are in Chestertown. This property is in a historic area, an easy walk to the river, the historic district, shops, a nature center, park, and many restaurants. It is an easy drive to anywhere requiring a car and parking is available and convenient. We highly recommend!
Stayed 2 nights in Nov 2025

10/10 Excellent

Verified traveler

Liked: Cleanliness
Perfect quaint property! everything you would need provided except we didn’t realize there was no TV but that was us not the property. Highly recommend. great location. walk to everything Chestertown.
Stayed 2 nights in Oct 2025

10/10 Excellent

Susan H.

Liked: Cleanliness
Very neat and clean. Quiet and private. Short walk to shopping and restaurants. Quick response from host when questions or recommendations were asked. No TV encouraged us to enjoy the outdoors.
Stayed 2 nights in Oct 2025

10/10 Excellent

kathleen d.

Liked: Cleanliness
This is a charming place. Beautifully furnished with no detail overlooked. We loved the artwork by local artists, the attention to sustainability, and the commitment to the community. The location was perfect - a few minutes walk to the shops and restaurants and the Saturday farmers' market. One of the best we had ever visited!Communications with the owners and check-in were smooth. We hope to return.
Stayed 2 nights in Sep 2025

10/10 Excellent

Michele R.

Liked: Cleanliness
Wonderful weekend in Chestertown - perfect location!
Stayed 2 nights in Aug 2025

10/10 Excellent

Peggy K.

Liked: Cleanliness
Stayed 3 nights in Jul 2025

10/10 Excellent

Tiffany c., St. Thomas, VI

Liked: Cleanliness
As others have noted, the space is very clean, well appointed and conveniently located. I'd like to add that the hosts have done a wonderful job of representing the community in the home. Their art collection is lovely and features local artists. The books placed are all interesting and about the area; even the chocolates were purchased from a locally owned store. I would absolutely stay here again and highly recommend it.
Stayed 5 nights in Jul 2025

10/10 Excellent

Verified traveler

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond.
Stayed 2 nights in Jul 2025

8/10 Good

Cynthia S.

Liked: Cleanliness
Loved the location and ease of access to downtown. Property was super clean, organized and beautifully appointed with original art too.
Stayed 2 nights in Jun 2025

8/10 Good

Carlos, Monroe Township

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
Very quiet area and well kept properly. The unit very clean and well kept, the Internet is pretty good with good reception, what I like the most was that it was so close to everything with restaurants and museums close by the park that hosted most of the events was close enough for a short walk and all sort of streets that held events were close by, this is a great location of the memorial day events and I have to say the honest were great and very helpful.
Stayed 3 nights in May 2025

10/10 Excellent

Amanda D.

Liked: Cleanliness

Nice place to stay!

Very nice little apartment with a separate entrance from the main house. It was furnished and decorated very nicely (it didn't feel like a generic rental but it wasn't so fancy you were afraid to use stuff). Comfortable bed, nice pillows, nice sheets. I loved the porch and garden (and occasional visits from their very cute dog).
Stayed 2 nights in May 2025

10/10 Excellent

Brian W.

Liked: Cleanliness

Immaculate and charming space!

Weekend stay from Philly. Everything was perfect for the two of us. The space is so inviting with a beautiful outdoor garden and sitting area. Quiet, impeccably maintained and stocked with every detail that we needed. Outstanding hosts. Can’t wait to visit Charlestown annd stay here again!
Stayed 2 nights in May 2025

10/10 Excellent

George

Liked: Cleanliness, amenities, property conditions & facilities
Very nice place. Great location, close to dining, etc. No TVs. Would have liked to know that going in. Otherwise, prefect spot.
Stayed 2 nights in May 2025

10/10 Excellent

Verified traveler

Liked: Cleanliness

Great chill stay

Stephen & Marianna were great hosts! They gave recommendations for what was nearby for food and drinks and made us feel at home. the space was great and sitting on the patio was very pleasant. They are centrally located so it was very easy to park the car and walk to the main downtown. Would 100% stay again!
Stayed 2 nights in Apr 2025

10/10 Excellent

Lindsey C.

Liked: Cleanliness

Our stay for War on the Shore

Your guest house was perfect. It had everything we needed. Short walk to town and the Chester River. Will definitely book again when we come to town for our son’s lacrosse games!
Stayed 2 nights in Apr 2025

10/10 Excellent

June M.

Liked: Cleanliness

Quite nice!

Property is clean & comfortable. Great location for walking to downtown Chestertown shopping and restaurants.
Stayed 2 nights in Apr 2025

10/10 Excellent

Tammy S.

Liked: Cleanliness

Perfect little gem in the heart of Chestertown

We loved staying at Stephen and Marianna’s fantastic home. The space is bright and well-decorated, it’s private and had all of the amenities we needed. The location is wonderful and we were able to walk a couple of blocks to the stores and restaurants and enjoyed the Saturday morning farmers market. When we checked in, the keypad wasn’t working but within about a minute, Stephen appeared and let us in so it was all very easy and nice. Highly recommend staying here - perfect for a couple to do a weekend getaway!
Stayed 2 nights in Mar 2025

10/10 Excellent

Hillary K.

Stayed 7 nights in Oct 2024

10/10 Excellent

Karen W.

Liked: Cleanliness

Perfection - you won't want to leave

This is the second time I stayed here and will be back. I was able to work from here and enjoyed breakfast and lunch on the covered porch with a sweet companion (the owners' totally chill dog). Walking distance to everything. Check out the new wetland preserve at the end of the street.
Stayed 3 nights in Nov 2024

10/10 Excellent

Mary Pat

Liked: Cleanliness, property conditions & facilities
The cottage was comfortable and welcoming. It was close to restaurants, the Farmers' Market and delightful shops and galleries.
Stayed 2 nights in Oct 2024

10/10 Excellent

Julia D.

Liked: Cleanliness

Sweet serene spot in the heart of Chestertown!

We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!
Stayed 3 nights in Aug 2024

10/10 Excellent

June M.

Liked: Cleanliness

Perfect place!

This property was so accessible to everything we wanted to do and the accommodations perfect for the two of us. It was like a home away from home comfortable and clean! Even the pillows were perfect! We would highly recommend.
Stayed 2 nights in Sep 2024

10/10 Excellent

alex d.

Liked: Cleanliness

Amazing experience

We had such a sweet & relaxing stay at this garden oasis. It was equipped with everything we needed and we cannot wait to be back.
Stayed 2 nights in Aug 2024